Konformacijska analiza peptidomimetika izvedenog iz alanina, fenilalanina i ferocen-1,1'-diamina

undergraduate thesis

• Title (english): Conformational analysis of peptidomimetic derived from alanine, phenylalanine and ferrocene-1,1'-diamine
• Author: Laura Jelaska
• Mentor: Monika Kovačević (mentor)
• Granter: University of Zagreb; Faculty of Food Technology and Biotechnology; (Department of Chemistry and Biochemistry); (Laboratory for Organic Chemistry); Zagreb
• Defense date and country: 2023-07-14, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Nutrition

Abstract

Ferocen je sendvič spoj koji se sastoji od dva paralelna ciklopentadienilna prstena između kojih se nalazi atom željeza. Zbog svojih povoljnih svojstava koristi se kao kalup pri sintezi peptidomimetika. Peptidomimetici su spojevi koji imaju sposobnost imitiranja sekundarne strukture proteina. Upotreba peptidomimetika je od iznimne važnosti, budući da se peptidi i proteini, zbog svojih brojnih nepovoljnih svojstava, ne mogu koristiti u kliničke te terapeutske svrhe. Jedan od načina pripreme peptidomimetika je „umetanje“ ferocenskog kalupa u peptidni lanac. Ciklopentadienilni prstenovi ferocena nalaze na udaljenosti od 3,3 Å, što omogućuje stvaranje intramolekulskih vodikovih veza između dva peptidna lanca, vezana na ferocen. Cilj ovog Završnog rada bio je, iz ferocen-1,1'- diamina i aminokiselina L-alanin i L-fenilalanin, sintetizirati peptid, Ac-L-Ala-NH-Fn-NH-L-Phe-Boc (1). Upotrebom infracrvene spektrometrije te nuklearne magnetske rezonancije učinjena je spektrometrijska analiza peptida 1, kako bi se dobile informacije o prirodi nastalih vodikovih veza. Dokazano je da u pripravljenom peptidu dolazi do tvorbe dviju interlančanih vodikovih veza koje induciraju tvorbu γ-okreta.

Abstract (english)

Ferrocene is a sandwich compound consisting of two parallel cyclopentadienyl rings with an iron atom in the middle. Due to its favorable properties, it is used as a form in the synthesis of peptidomimetics. Peptidomimetics are compounds that have the ability to mimic the secondary structure of proteins. The use of peptidomimetics is extremely important, because peptides and proteins cannot be used for clinical and therapeutic purposes due to their many unfavorable properties. One method of preparing peptidomimetics is to "insert" a ferrocene template into a peptide chain. The cyclopentadienyl rings of ferrocene are located at a distance of 3,3 Å which allows the formation of intramolecular hydrogen bonds between two peptide chains attached to ferrocene. The aim of this work was to synthesize the peptide, Ac-L-Al-NH-L-Phe-Boc (1) from ferrocene1,1-diamine and the amino acids L-alanine and L-phenylalanine. Infrared spectrometry and nuclear magnetic resonance were used to perform spectrometric analysis of peptide 1 to obtain information on the nature of the hydrogen bonds formed. Two hydrogen bonds are formed between the chains, which induce the formation of γ-turn in the prepared peptide 1.

• Keywords: ferocen; peptidomimetici; fenilalanin; vodikova veza; spektroskopska analiza
• Keywords (english): ferrocene; peptidomimetics; phenylalanine; hydrogen bond; spectroscopic analysis
• Language: croatian
• URN:NBN: urn:nbn:hr:159:134599
• Study programme: Title: Nutrition; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) nutricionizma (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) nutricionizma)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2024-04-16 11:20:38